Cyanoethylhydrazide in the preparation of nitrogen heterocycles. III. Heterocyclic 7-rings through the reaction of 1,3-dicarbonyl compounds with cyanoacetylhydrazide was written by Ried, W.;Kocher, E. U.. And the article was included in Angewandte Chemie in 1958.Electric Literature of C6H9N3O This article mentions the following:
Acetylacetone with cyanoacetylhydrazide in alc. in the presence of a few drops AcOH gives the mono(cyanoacetylhydrazone) (I), m. 165-6°, very soluble in dilute NaOH. The addition of at least 2 moles aqueous NaOH solution to I followed by acidification of the resulting yellow solution with AcOH yields MeC:C(CN).C(OH):N.N:CMe.CH2 (or ketone) (II), yellow, m. 237-8°, very soluble in dilute NaOH, soluble in dilute HCl. With HNO2, II gives orange leaves, m. 183-4°. In the same way, benzoylacetone and cyanoacetylhydrazide give PhCOCH2CMe:NNHCOCH2CN, (III), m. 122-3° soluble in dilute NaOH. 1-Cyanoacetyl-3-methyl-5-phenylpyrazole, m. 153-4°, may be prepared by treating III with aqueous alc. HCl. III with base yields PhC:C(CN).C(OH):N.N.CMe.CH2 (or ketone), light yellow needles, m. 257-8° soluble in dilute NaOH and dilute HCl, gives red needles, m. 216-17°, with HNO2. In the experiment, the researchers used many compounds, for example, 3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5Electric Literature of C6H9N3O).
3,5-Dimethyl-1H-pyrazole-1-carboxamide (cas: 934-48-5) belongs to pyrazole derivatives. Pyrazole has two ring nitrogen atoms in which N1 is pyrrolic and N2 is pyridine-like. The N1 nitrogen is not reactive but is deprotonated in the presence of a base-forming anion. Pyrazoles are commonly used scaffold molecules in drug discovery projects. The use of pyrazole derivatives is based on their analgesic, anti-inflammatory, antipyretic, antiarrhythmic, sedative, muscle relaxant, neuroleptic, anticonvulsant, monoamine oxidase inhibitory, antidiabetic and antibacterial activities.Electric Literature of C6H9N3O
Referemce:
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics